cis-1-benzyl-4-formyl-3-<(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl>-2-azetidinone

Base Information

• Chemical Name: cis-1-benzyl-4-formyl-3-<(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl>-2-azetidinone
• CAS No.: 110289-27-5
• Molecular Formula: C₂₀H₁₈N₂O₄
• Molecular Weight: 350.374
• Mol file: 110289-27-5.mol

Synonyms:cis-1-benzyl-4-formyl-3-<(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl>-2-azetidinone

Chemical Property of cis-1-benzyl-4-formyl-3-<(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl>-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-1-benzyl-4-formyl-3-<(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl>-2-azetidinone

There total 20 articles about cis-1-benzyl-4-formyl-3-<(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl>-2-azetidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(R)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)acetyl chloride (112674-71-2) → cis-(3R,4R)-1-benzyl-4-formyl-3-<(4R)-2-oxo-4-phenyloxazolidin-3-yl>azetidin-2-one (110289-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) toluene, 0 deg C, 2 h; room temperature, overnight

2: 1.) p-TsOH*H₂O, 2.) NaIO₄ / 1.) THF, H₂O, reflux, 6 h, 2.) Me₂CO, H₂O, 0-5 deg C, 1.5 h

With sodium periodate; toluene-4-sulfonic acid; triethylamine;

DOI:10.1021/jo9612180

Reference yield:

(R)-3-[(2S,3R)-2-((S)-1-Amino-2-hydroxy-ethyl)-1-benzyl-4-oxo-azetidin-3-yl]-4-phenyl-oxazolidin-2-one → cis-(3R,4R)-1-benzyl-4-formyl-3-<(4R)-2-oxo-4-phenyloxazolidin-3-yl>azetidin-2-one (110289-27-5)

Guidance literature:

With sodium periodate; In water; acetone; for 24h; Ambient temperature;

DOI:10.1021/ja00050a016

Reference yield:

(R)-3-[(2S,3R)-2-((R)-1-Amino-2-hydroxy-ethyl)-1-benzyl-4-oxo-azetidin-3-yl]-4-phenyl-oxazolidin-2-one (316821-35-9) → cis-(3R,4R)-1-benzyl-4-formyl-3-<(4R)-2-oxo-4-phenyloxazolidin-3-yl>azetidin-2-one (110289-27-5)

Guidance literature:

With sodium periodate; In water; acetone; for 24h; Ambient temperature;

DOI:10.1021/ja00050a016

upstream raw materials:

(3S,4R)-1-benzyl-3<(S)-4-phenyloxazolidinyl>-4-styrylazetidin-2-one

2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid

2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride

ethyl 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetate

Downstream raw materials:

1-benzyl-3β-[(S)-4-phenyloxazolidin-2-one-3-yl]-4β-hydroxymethylazetidin-2-one

(4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone

(2S,3S)-1-Benzyl-4-oxo-3-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-azetidine-2-carboxylic acid